Adolf Dehn's artistic career began after winning a scholarship to the Art Students League in New York. He traveled extensively, living briefly in Paris, Berlin and Vienna, absorbing the lessons learned modern European masters. He associated himself with the German Expressionist printmakers. George Grosz, the German socially critical printmaker, once said to Dehn, "You will do things in America which haven't been done, which need to be done."

Back in the states, Dehn worked during the 1920s and 1930s alongside other superb satirists as Peggy Bacon and William Gropper, sharing their love of commenting on the preposterous quality of life at that time. He was equally praised for his use of landscape to represent a generalized observation often ridiculing everything he sees, but does so with a human sympathy that lifts his lithographs out of the realm of burlesque.